Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors

Junyi Zhang, Chiyi Xiong, Jinfa Ying, Wei Wang, Victor J. Hruby

Research output: Contribution to journalArticle

42 Scopus citations

Abstract

(Matrix presented) The novel dipeptide β-turn mimetic, 4,8-disubstituted azabicyclo[4.3.0]nonane amino acid ester (15), has been synthesized to serve as a peptide mimetic of the dipeptide Phe-Arg, which contains two important pharmacophore elements in melanotropin peptides. Introduction of side-chain functionality at C-8 was achieved by using β-functionalized pyroglutamate (8) as a synthetic precursor. The side chain at C-4 was introduced by bromination of dehydroamino acid intermediate (10) followed by Suzuki cross-coupling.

Original languageEnglish (US)
Pages (from-to)3115-3118
Number of pages4
JournalOrganic Letters
Volume5
Issue number17
DOIs
StatePublished - Aug 21 2003

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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